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By Peter Abraham, Globe Staff

BALTIMORE — The Red Sox lost 90 games in 1966. Young sluggers Tony Conigliaro and George Scott had good seasons for manger Billy Herman before he got fired, but the pitching staff had a rough time of it.

In the 45 years since, the Sox fielded plenty of teams that disappointed a generation of fans. But until Sunday, none had lost 90 games.

Zach Stewart pushed the Sox deeper into despair, getting hit hard again in a 6-3 loss against the Baltimore Orioles.

“We haven’t had a good season and every loss hurts, all 90 of them,” said Bobby Valentine, who is almost surely three games away from losing his job.

Stewart allowed five runs before being pulled out of the game in the third inning. The skeleton Sox lineup — Mauro Gomez batted fourth and Danny Valencia fifth — was unable to overcome that kind of deficit and the Sox lost their fifth straight.

At 69-90, the Sox have the third-worst record in the American League and are 23 games out of first place.

Stewart, a 26-year-old righthander, was obtained from the White Sox in June for Kevin Youkilis. The Sox must have liked something about him, but it hasn’t been apparent what that could be in two starts.

In games against the Angels and Orioles, Stewart has allowed 14 earned runs on 17 hits over 5.2 innings. Counting his time with the White Sox, Stewart has surrendered 14 home runs over 35.2 innings this season.

In 14 career starts in the majors, Stewart is 2-9 with a 7.51 earned run average.

Also:

• Clayton Mortensen allowed one run in 3.1 innings of relief. He has a 2.93 ERA over 40 innings and earned a look next season. “He’s been terrific. He’s very competitive and he throws pitches that are tough to time,” Valentine said.

• The Sox finished 5-13 against the Orioles. They have lost 19 of 26 against Baltimore. … The Sox were 7-19 in September a year after their infamous 7-20 September collapse. … The Sox are 26-47 since the All-Star break and 104-127 since the All-Star break in 2011.

• The Sox had their rookies dress up for the train trip to New York. Most teams have themes for this sort of thing and plan it out. The Rays, for instance, had their rookies dress in colorful leotards and choreograph a dance to "Call Me Maybe" that was performed on the field at Fenway Park.

The haphazard Sox had most of the rookies wear cheerleader outfits with Will Middlebrooks dressed as Dorothy from the “Wizard of Oz.” The outfits were cheap Halloween costumes and if much thought went into the hazing ritual, it was very little.

The larger point is that the Sox are so disjointed and lacking in leadership that even something silly like rookie hazing comes off poorly.

• A little "good" news: With the loss, the Red Sox are guaranteed of receiving one of the top nine pick picks in the amateur draft next June. That is important for reasons beyond the opportunity to add a premium player.

Under the rules of the new collective bargaining agreement, the first 10 picks in the draft are protected from being surrendered as compensation for signing a top-tier free agent.

Now, if the Sox were to sign such a free agent, they would give up only their second-round choice.